


Sleeping with the Boss

by ratherbehere



Series: Adventures in Porn Tropes [1]
Category: Supernatural
Genre: Blow Jobs, Come Swallowing, Hand Jobs, M/M, Mildly Dubious Consent, Plot What Plot/Porn Without Plot, Secretary Dean
Language: English
Status: Completed
Published: 2014-09-18
Updated: 2014-09-18
Packaged: 2018-02-17 22:34:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,949
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2325608
Author URL: https://archiveofourown.org/users/ratherbehere/pseuds/ratherbehere
Summary: <blockquote class="userstuff">
              <p>Dean's about to get fired and he can't let that happen. Maybe he can make it up to his boss, keep his job? </p>
<p>Or maybe there's more to the story.</p>
            </blockquote>





	Sleeping with the Boss

**Author's Note:**

> This is the beginning of a series of blatant porn heavy one shots that will all be classic porn setups, with various degree of spin on the trope. There will be both destiel and cockles fics, whichever strikes my fancy, with possible polyamorous relationship to come later, if requested.
> 
> As this trope often contains consent issues, please know that this fic does contain those tones, but I also did my best to make it fully consensual as well. In other words, it starts as implied sex for a job, it happens because of desire. If you feel I need to upgrade my warnings, please let me know.

“Dean Winchester,” Castiel says through his open office door. The deep, gravelly voice reverberates all the way to Dean’s desk and he shudders. He knows that tone. He is in deep, deep shit. “Come here.”

Dean stands up shakily, smooths his shirt. Castiel had waited until the end of the day when almost everyone had left to call him back. That meant that whatever this was, it was not good. He swallows hard before moving to the office door.

“Shut the door,” Castiel commands. Dean pushes it shut, the door clicking into place. “Sit down.”

Dean maneuvered stiffly into the seat. “Did I-“ he begins and has to swallow again before he can continue. “Is everything okay?”

Castiel moves, perches on the edge of desk, arms crossed. It’s like a particularly grumpy bird is staring down at him, ready to peck his eye out.

“Frankly, no,” Castiel tells him. “You misfiled my paperwork.”

Dean gulps. “I can fix it-“

“Let me finish,” Castiel cuts him off coldly. “You didn’t return two phone calls I asked you to follow up on. You were late twice this week alone.” Dean’s heart is sinking quickly. This is all true, and he knows it. “Mr. Winchester, your performance is lacking.”

Dean’s eyes are glued to the tips of Castiel’s polished black business shoes. “Sir,” he finally manages to get out. “If I could explain, my brother-“ 

His brother broke his arm over the weekend. It had made Dean late when Sam had needed extra help in the mornings that he hadn’t been prepared for. He’d gotten sloppy because he was freaked out.  
Not only was he naturally preoccupied, worried about Sam healing okay, but Sam couldn’t work while he was injured, and they’d barely been making the bills as it was. It was the truth, but it all sounded like excuses, even in his ears. To his strict and no-bullshit boss, it would sound pathetic.

“I am responsible for 2.2 million dollars worth of customers and assets Mr. Winchester, unless your brother passed away and you somehow failed to apply for FMLA, I can’t afford the luxury of caring about your personal issues. You’ve gotten careless and I’ll have to let you-“

“No!” Dean shouts, panicked. He hates sounding so desperate and weak, but, well, he is. He needs this job or him and Sam will be on the streets by the end of the month. “Please,” he says, sliding to his knees. “I swear, I will be better now, I’ll never have an issue like this again.” Castiel seems to consider this, or at least doesn’t outright dismiss him, which is a minor blessing. “Is there any way I could make it up to you?” he asks, looking up to give Castiel his best puppy dog eye. 

He didn’t mean for it to sound so lewd. He had meant he could clean Castiel’s apartment or wash his car. But kneeling on the ground, looking up into Castiel’s wide, blue eyes, slowly becoming more black than blue, he realizes how the offer had come across.

And he’s entirely okay with that.

The truth is, he doesn’t know his boss that well. He’d only been working for him for a few months, which is probably why he was so willing to let Dean go, he hasn’t really proved himself yet. But you didn’t have to know the guy on a personal level to know he is hot. And while he could be strict, he was cool and in command of himself and those around him at all times. Dean could be intimidated by him at the same time he was fighting off a boner under his desk.

Castiel hasn’t replied yet, but he licks his lips, and Dean considers that a good sign. He shifts forward on his knees, placing himself right at Castiel’s feet. When Castiel doesn’t stop him, Dean slides his hands up the back of his thighs, watches as Castiel swallows hard.

When Dean unbuckles Castiel’s belt and he still hasn’t spoken or responded in anyway, Dean has a moment of panic. What am I doing, he thinks frantically.

Giving a hot guy a blow job so I can keep my job.

Win – win, right?

Castiel waits until Dean has his blood filled cock exposed to the air before he hisses and puts a hand firmly on Dean’s shoulder. 

“Dean, are you sure about this?” he asks. “I won’t force you to-“

“I need this job,” Dean asserts.

“You don’t have to suck my cock to keep your job, we can talk. I didn’t realize you were so desperate. Maybe I was a bit hasty.” He reaches for his zipper. “Tell me what’s going on.”

Oh hell, now the cool, composed, powerful, hot man is going to add compassionate to the list?

“Oh hell no,” Dean says from the floor, his hand stilling Castiel’s.

“Excuse me?” Castiel asks with an arched eyebrow.

“Can we talk after I suck your cock?” Dean asks bluntly, giving Castiel a cheeky grin. “Please, sir, let your secretary be a naughty boy and suck your cock.”

Castiel groans loudly at that, his hand falling away from his zipper. Not one to miss an opportunity, or a sign, Dean grips his cock tightly at the base and sucks the tip into his mouth. He pauses, looking up to Cas through his eyelashes, catches him breathing irregularly, eyes blown wide and shocked.

He keeps the eye contact as he slides down Castiel’s length, letting the velvety skin drag a little on his lips before they inevitably pick up more saliva. Dean moves sinfully slow, until his lips are at the base of Castiel’s cock and the man above him lets out a whine. Castiel rests a hand in his hair. Dean can feel his fingers twitching, a desire to clench being carefully restrained.

He curls his tongue around the shaft, works his throat and cheeks, sucking hard, until he has to pull up just a bit, just enough to catch his breath.

Dean repeats this process a few times before he pulls off completely and looks back up to Cas. “You can fuck my throat if you want,” he says, his voice already raw. “I like it.” Castiel gives him a dubious look. “I swear, Cas, I’m not saying that for a raise or anything. Fuck my throat.”

He lets the use of the nickname slide off his tongue on purpose. Castiel doesn’t miss it. He groans hard in response.

“Fuck,” he whispers. Dean’s boss has never sworn before.

Taking Cas’s cock back between his lips, he wiggles his eyebrows. Castiel adds his other hand to Dean’s hair, tightens the grip, and slowly pushes him down until Dean’s lips are seated at his base once again. He pulls his hips back just a bit and thrusts gently forward. When Dean doesn’t gag, he does it again, again, until he’s thrusting his hips and pulling and pushing with his hands so hard and fast that Dean’s eyes do eventually begin to water. 

He wasn’t kidding though, when he said he liked it. His pants are so tight, it hurts. He didn’t even know it was possible for boxers to feel that constricting. Still, he ignores it, focuses on working his tongue and providing some suction. 

Castiel is panting hard now, the musky smell from his junk is getting stronger as he sweats a little. Dean takes a small risk, brings his hands up to cradle Castiel’s balls. He has to push some cotton down so the grip is not too shocking, but it’s enough for his boss to let out a strangled cry. 

“Oh fuck,” Castiel mumbles, completely lost in sensation, his movements erratic. “Dean, Dean, oh god, Dean.”

Experimenting again, Dean pulls down just slightly on Castiel’s balls, and with a yelp, the man comes hard. Come hits the back of Dean’s throat and he lets it slide down, sucking at Castiel’s cock like it’s a candy filled straw. 

Once Castiel has finished, Dean has to tap Castiel’s hips to get him to release his head.

“Oh, I’m sorry,” Castiel says quickly, releasing his fists from Dean’s hair. 

“S’okay,” Dean rasps out. He stands up, wobbly legs barely working. He’s about ready to collapse into the chair behind him when a hand grips his erection tight. 

Dean wavers then, about to fall, when Castiel spins them, pinning Dean to the desk. Before he can properly process that his boss is now pulling his cock out of his embarrassingly damp boxers, there’s already a hand wrapped around the member, twisting and stroking with a controlled deftness that makes Dean’s head spin.

He hisses, “Coming,” barely getting the warning out just seconds before he’s spilling over Castiel’s fist, thrusting weakly into the gorgeous fingers he may have admired a time or two before.

When he’s done spilling and reality is starting to come back into focus, Castiel removes his hand and reaches for a tissue from the box on the desk. He cleans his hand, throws the tissue away, and reaches for another. Then he cleans the come that had dribbled onto Dean’s skin too, and who would have thought he could be so tender?

Then the rich and powerful Castiel Milton collapses into the chair Dean had not 15 minutes ago been sitting in and laughs. 

He laughs and laughs until tears are falling from his eyes. Dean frowns. He has no idea how this could be funny.

“I’m sorry,” Castiel says, whipping a tear away. “It’s just. I don’t think this is what my dad had in mind when he told me not to sleep with the secretary.” Dean smirks. Yeah okay, he’s not exactly your typical sexy tall blonde with a perky rack, a low neckline, and a pair of heels. 

Actually, he kind of is, just minus the rack and heels.

“You can’t be my secretary any more, of course.”

Dean’s gut falls so fast he nearly throws up. “What?!” he demands. “What happened to talking about this?! Jesus, I just sucked you off and now you’re letting me go? How many times have you done this? Used your secretary and fired him before he could-“

“Dean!” Castiel shouts, to interrupt him. He continues more calmly, “Dean, you can’t be my secretary. But I’ll have Hester take you on.” 

Dean’s head is spinning. Castiel sighs and stands up. He places a palm on Dean’s cheek. “I can’t be fucking my secretary,” Castiel says. “And even if you wanted this to be the only time we do this, I don’t want it to be. You’d be a distraction for me.” He smiles. “You already were, this would just make it worse.”

“Seriously?” Dean asks, a grin breaking out. “Wait,” he stops, his brain picking up the thread. “Hester is in charge of sales.”

“Yes she is. She’ll train you as a salesman, not that you’ll need much help. And you’ll be paid significantly better,” Castiel says with a knowing look. “Is that a problem?”

Dean wraps his hand around Castiel’s tie and pulls him into a deep kiss. The man’s lips are plush and he kisses with just the right amount of pressure and tastes clean and fresh and Dean knows he’ll be wanting to kiss Castiel as many times as he can.

“Is it a problem that I think you’re gorgeous and want to learn everything about you, including how your fingers feel up my ass?” Dean asks back.

Castiel laughs, curls his hand around the back of Dean’s head and brings it forward, letting their foreheads touch. 

“Don’t ask stupid questions,” he replies with a grin.

And well. That was kind of his point.


End file.
